Implementing CA signed SSL certificates with vSphere 5.x – Part 4 – VUM and vCO/vRO

19/04/2015

In the previous post, we discussed the replacement of SSL certificates in the vCenter Server Appliance. Following our planning, next on the list is the vSphere Update Manager and the vCenter Orchestrator Appliance.

vSphere Update Manager

Our guide is “Configuring CA signed SSL certificates for vSphere Update Manager in vCenter Server 5.1 and 5.5 (2037581)”.

One important note from this KB: “You can replace only the SSL certificates that Update Manager uses for communication between the Update Manager server and client components.
You cannot replace the SSL certificates that Update Manager uses on port 9087 when importing offline bundles or upgrade release files.

KB 2037581 resumes at the point where we ended in Part 2, and created the required SSL certificates.

Steps:

  • Assuming the VUM is a VM, create a snapshot before you start working.
  • If you haven’t already done this, import the root certificate Root64.cer into the “Trusted Root Certification Authorities” Windows certificate store. This ensures that the certificate server is trusted from now on.
    SSL-04-01
    Figure 1
  • Backup the current certificates, location: C:\Program Files (x86)\VMware\Infrastructure\Update Manager\SSL directory.
    SSL-04-02
    Figure 2
  • Copy the new certificate files to this directory replacing the current ones. If you are following my blog posts, the certificates are located in C:\certs\UpdateManager.
  • Stop the vSphere Update Manager Service and the vSphere Update Manager UFA services from the services control manager.
  • Launch the exe application, located in C:\Program Files (x86)\VMware\Infrastructure\Update Manager.
    While using the VCSA, the VUM is always separated, so use the IP address or hostname of the vCSA. Use the credentials Update Manager uses to connect to the VCSA.
    SSL-04-03
    Figure 3
  • Click the SSL Certificate Link.
  • Select the Followed and verified the steps.
  • Click Apply.
    SSL-04-04
    Figure 4
  • Click OK when prompted with message “Restart the VMware vSphere Update Manager service to apply the setting”.
  • Restart the vSphere Update Manager Service and the vSphere Update Manager UFA services.

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Implementing CA signed SSL certificates with vSphere 5.x – Part 3 – vCenter Server Appliance

11/03/2015

In the previous post, we highlighted the default template needed, in case of an Organizational CA, and ended with the creation of the certificates needed for the vCenter Server components.

According to our compass KB “Implementing CA signed SSL certificates with vSphere 5.x (2034833)”, the next step is to replace the vCenter Single Sign-On certificate and it points us to KB “Configuring CA signed SSL certificates for vCenter Single Sign-On in vSphere 5.5 (2058519)”.

Unfortunately, we are in trouble now, as KB 2034833 refers to the Windows vCenter Server components, with no reference to the vCenter Server Appliance. We will return to this KB later, for the vSphere Update Manager.

Luckily, KB “Configuring Certificate Authority (CA) signed certificates for vCenter Server Appliance 5.5 (2057223)” is available for the vCenter Server Appliance. In fact this KB contains all steps for setting up OpenSSL, generating certificate requests, getting and implementing certificates.

The Script

In fact, we have reached the section “Installation and configuration of the certificates for all the components”. This 40 step long section contains a lot of commands. To overcome the differences and make the installation process easier, I have created a script which can be found in this post. Copy and paste the content in a notepad and save as vcsa_certs.sh.

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Implementing CA signed SSL certificates with vSphere 5.x – Part 2 – Obtaining Certificates

11/03/2015

Implementing CA signed SSL certificates with vSphere 5.x – Part 2

This is the second post in a series about implementing CA signed SSL certificates. The previous post provided some background and a few important questions to consider before taking off.

Until now, KB “Implementing CA signed SSL certificates with vSphere 5.x (2034833)” is our compass.

Creating a new default template

If you are using certificates from an organizational CA, like I am, the first step is to create a correct SSL certificate template for the Certificate Authority. Follow the directions in KB “Creating a Microsoft Certificate Authority Template for SSL certificate creation in vSphere 5.x (2062108)”.

The steps in this KB are straightforward. After creating a new default template, the new template needs to be added to the Root CA or Subordinate CA server. This new template should be used in place of the Web Server template.

There are a few important steps:

  • Create a duplicate of the Web Server
  • On the Extensions tab, Key Usage, make sure you select the Signature is proof of origin (nonrepudiation) option and the Allow encryption of user data
    SSL-02-01
    figure 1
  • On the Extensions tab, Application Policies, make sure you Add Client Authentication.
    SSL-02-02
    figure 2

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Implementing CA signed SSL certificates with vSphere 5.x – Part 1- Introduction

09/03/2015

Why certificates?

Almost all vSphere components, like ESXi, vCenter Server, vSphere Update Manager make use of SSL certificates. However, the certificates installed during the installation process are signed by VMware and are not verifiable and are not signed by a trusted certificate authority (CA).

SSL-01-01Figure 1

Also the vSphere Hardening Guide (for all components) recommends not using the default self-signed certificates for ESXi communication for all three profiles, because;
Using the default self-signed certificates leaves the SSL connection open to Man-in-The-Middle (MiTM) attacks. Replace default self-signed certificates with those from a trusted CA, either commercial or organizational.

The vSphere Hardening Guides recommends the following assessment procedure and if you need to replace SSL certificates points to a useful KB.

Connect to each ESX/ESXi host with an internet browser,
https:// <hostname>/. View the details of the SSL certificate; determine if it is issued by a trusted CA, either commercial or organizational. To change SSL certificates refer to KB “
Implementing CA signed SSL certificates with vSphere 5.x (2034833)”.

See figure 1, for a result.

The vSphere Hardening Guide points to the very useful KB 2034833, but it also becomes clear that it’s one of many KB s on implementing SSL certificates, and there are even more KB s not mentioned.
So, I was very curious how this would work out in a common vSphere Cluster.

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vExpert 2015

06/02/2015

On February 5th, the list 2015 vExperts was announced by Corey Romero and the VMware Social Media & Community Team.

As stated in the announcement; “…and point out that a “vExpert” is not a technical certification or even a general measure of VMware expertise. The judges selected people who were particularly engaged with their community and who had developed a substantial personal platform of influence in those communities.

For the third time in a row, I have been selected for my (modest) contribution to the amazing VMware community. I feel proud, honoured and humbled at the same time.

Congratulations to all the other vExperts! Let’s continue and make it an awesome 2015.
The announcement and the complete list of vExperts can be found here.

I would like to thank all of you for making this possible.


VCAP5-DCA exam VDCA550 – Complete

01/02/2015

The complete Study Guide for VCAP5-DCA exam VDCA550 is now available. Over 300 pages, covering all Sections.

Download: VCAP5-DCA exam VDCA550.

If you have any questions or remarks, please respond. Thank you very much for reading.

 


VCAP5-DCA exam VDCA550 – Section 6

15/01/2015

Almost there…
Section 6 of the Study Guide for VCAP5-DCA exam VDCA550 is now available. Over 20 pages, covering all Section 6 objectives.
The download also includes previous sections!

Download VCAP5-DCA exam VDCA550 – Section 1-6.

If you have any questions or remarks, please respond. Thank you very much for reading


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